Sissy Baby Steps

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Small baby steps from a regular man to a sissy.
1.5k words
4.3
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It has been a long day at work... as usual. I usually come at about 19:00 and help my wife with the kids. It is the regular stuff like showers, supper, a bit of homework the kids forgot and a bit of play time. The kids go to sleep till about 21:00 or even 21:15. The my wife opens the T.V. in the living room and I sit on the dining table with my laptop on catching up on some "urgent" work related issues. Years ago we had great communication - I and my wife - but in the last years the conversations reduced to logistics mainly.

At a certain point at about 23:00 my wife gives up, says quietly good night and goes to the bedroom. This is the time I continue working. Clearly the work ever ends, but this is clearly an excuse to wait till me wife falls asleep. At midnight I usually go to the bathroom and then patrol the house and check that the wife and kids are sleeping. I sit with my back against the wall facing the corridor leading to the bedroom and the children room. I put on my earphones, left side on my ear and right side behind my ear so I can hear the laptop sound and hear any noise in the house. Then I open my personal laptop with the work laptop open just to show I am still busy. I open the browser in private mode and open my favorite porn site filled with categories and the party begins.

I usually start with looking at big tits and then huge tits videos. Quickly I loose interest and I want something more intense. My Dopamine is clearly having a hell of a party. I move on to interracial and gang bang videos with huge black heavy cocks pound a white chubby juicy pussy. The girl screams with pain and enjoyment begging for more. As I continue watching gang band after gang bang, penetration after penetration, cum after cum. And every time sooner or later I have realize I can never be like that.

I am a bit chubby, hairy with a with a barely 3 inch cock when fully erected. I think I measured 3 inches when the ruler left a mark tight above the base of my cock. So screams are not going to happen. When I had sex with my wife.. three or four years ago... she never screamed. She always said it was great sex and I played along. Once she laid on her side, raised a left foot up and told me to lay behind her and fuck her pussy from behind. It was a real mess. I tried so desperately to penetrate her pussy. I think I managed to barely touch her pussy lips with the head of my cock. After 3-4 long minutes had to change position so I can provide a better penetration.

So, as some strange self punishment I started seeing small penis videos. These videos changed to small penis humiliation videos, followed by cuckold videos, followed by sissy videos, followed by conditioning videos. I started seeing one video after another becoming a cuckold, becoming a sissy and becoming a fagot. I really love women, tits, pussies, chubby butts and all. But continuing seeings these conditioning videos gradually changed me. It became less interesting to watch a woman having sex. It was more rewarding to see a cock penetrating an ass hole with a tiny cock and balls flapping and bouncing fast. It was more appealing to see a beautiful mistress guiding me how I should suck cock and how I should dress up as a sissy.

At a certain point I had to stop and have a shower. My wife complained I enter the bed without a shower. I was great to have a shower and jerk off. I erased the history in the browser, closed the lights and gently entered the bathroom next to the bedroom where my wife sleeps. I close the door gently, get undressed and enter the shower. After I soap my self I start jerking off with my right hand facing the corner with my head slightly looking to the left so I can slightly see the bathroom door. I fantasize sucking all those big cocks and picturing my wife being fucked hard. Usually I cum, dry up, put on underwear and quietly go to bed next to my wife. But not this night... This night was special.

Hot water was streaming down, the bathroom was full of steam. My barely 3 inch cock was fully erected facing the wall with my hand stroking it hard... visualizing my wife fucked hard screaming with enjoyment.. and it is almost cumming... Ahhhh... I closed my eyes and the door bursted open. I immediately stop stroking my fully erected cock facing the corner and I give an Embarrassing smile to my wife.

"Turn around and face me now!" she demanded.

"What?!" I was trying to stall in order to give my cock time to relax.

"Come on, turn around. I know what you are doing every night." I was so embarrassed and slowly turned to face her. I wanted to hide the fact that I had an erection but I also did not like my wife staring at that barely one inch long so called cock. "Give me the water hand shower and put your hands on the sides of the shower." She reached out to me cock with a metal ring. I started to get really excited and scared at the same time. It was like a movie scene when you already know what is going to happen. She placed the ring around the base of my cock and balls. She opened the cold water right on me cock. My body was burning hot from the streaming water and now the shot of cold water hit my cock making it shrink almost half an inch. She reached out her other hand with a tiny cage and started pressing down towards the ring.

"Wait!... What are you...?" I said with a clear understanding what is happening. I did not move and waited for her to complete her procedure. It was as if my whole body wanted it while my inner self was screaming in silence. My wife pressed down the almost flat small cage down my cock. My cock tried to resist but my wife's delicate gentle and soft hands were gripping hard squeezing the last drop of power in my cock. My cock crushed into a tiny case and quickly my wife turned some key in there and the sound of a "click" marked that the battle was over.

My wife stood up and made a step back. Then she said "finish your shower and come to bed. It is very late. Do not forget to throw your dirty close in the laundry basket." I slowly turned around, opened the hot water as if nothing happened. My wife closed the door behind me and my hand was all over the chastity device pressing my cock flat and with my balls held a bit tight between the ring and the cage.

I realized I did not cum but I could not do anything about it. I was also scared to touch the chastity device. It felt awkward. I shut the water and dried up. I put on my underwear and T-shirt. I got out of the shower and slowly climbed up my side of the bed. My wife was asleep like nothing unusual happened.

My thoughts drove me crazy, my stomach was burning hot twisting inside itself. I laid straight in bed trying not to touch anything. It took me forever till I managed to fall asleep. I was thinking how to ask to get the key back or simply find a way to release myself from this predicament.

Waking up to the sound of my smartphone alarm clock, I reached out my hand to make sure it was all just a very vivid dream but there is was. My cock was still smashed into a tiny cage and my balls sticking out from the cracks. I heard my wife arranging the kids to school. I wanted to talk to her but one look and I realized I was expected to follow my usual routine as is.

I did everything as I was expected to do during that morning. Two things were very different. I had to sit down on the toilet seat to pee. The pee was splashing all over inside the toilet seat. My inner thighs also got very wet. In addition, it was a challenge to wear my pants scared not to touch the new home of my cock and balls.

I usually take the kids to the kindergarten and school and then continue to work. My wife waved and wished us a splendid day. Obviously the new condition distracted me from focusing on my tasks at work. One thing I knew for sure... I would not be working tonight.

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allaboutcontrolallaboutcontrolabout 1 hour ago

interested to see where this goes. Keep it up! :)

Royse69Royse694 days ago

Very good start, I hope you continue with the story

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